Literature DB >> 18646771

Brevisamide: an unprecedented monocyclic ether alkaloid from the dinoflagellate Karenia brevis that provides a potential model for ladder-frame initiation.

Masayuki Satake1, Andrea J Bourdelais, Ryan M Van Wagoner, Daniel G Baden, Jeffrey L C Wright.   

Abstract

The dinoflagellate Karenia brevis is known for the production of brevetoxins, a family of n class="Chemical">polycyclic ether toxins, as well as their antagonist brevenal. Further examination of organic extracts of K. brevis has uncovered yet another unprecedented cyclic ether alkaloid named brevisamide. This report describes the structure elucidation of brevisamide based on detailed MS and NMR spectral analysis, and the importance of this new compound in shedding light on the biogenesis of fused polyethers is discussed.

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Year:  2008        PMID： 18646771      PMCID： PMC2655204          DOI： 10.1021/ol801243n

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Biosynthetic origins and assignments of carbon 13 NMR peaks of brevetoxin B.

Authors:  M S Lee; D J Repeta; K Nakanishi; M G Zagorski
Journal:  J Am Chem Soc       Date:  1986-11-01       Impact factor: 15.419

2.  A new polyether ladder compound produced by the dinoflagellate Karenia brevis.

Authors:  Andrea J Bourdelais; Henry M Jacocks; Jeffrey L C Wright; Paul M Bigwarfe; Daniel G Baden
Journal:  J Nat Prod       Date:  2005-01       Impact factor: 4.050

3.  Biosynthesis of 13-desmethyl spirolide C by the dinoflagellate Alexandrium ostenfeldii.

Authors:  Shawna L MacKinnon; Allan D Cembella; Ian W Burton; Nancy Lewis; Patricia LeBlanc; John A Walter
Journal:  J Org Chem       Date:  2006-11-10       Impact factor: 4.354

Review 4.  The chemistry and biological function of natural marine toxins.

Authors:  T Yasumoto
Journal:  Chem Rec       Date:  2001       Impact factor: 6.771

5.  Structure of brevetoxin A (GB-1 toxin), the most potent toxin in the Florida red tide organism Gymnodinium breve (Ptychodiscus brevis).

Authors:  Y Shimizu; H N Chou; H Bando; G Van Duyne; J Clardy
Journal:  J Am Chem Soc       Date:  1986-02-01       Impact factor: 15.419

6.  Studies of the biosynthesis of DTX-5a and DTX-5b by the dinoflagellate Prorocentrum maculosum: regiospecificity of the putative Baeyer-Villigerase and insertion of a single amino acid in a polyketide chain.

Authors:  Gordon R Macpherson; Ian W Burton; Patricia LeBlanc; John A Walter; Jeffrey L C Wright
Journal:  J Org Chem       Date:  2003-03-07       Impact factor: 4.354

7.  Epoxide-opening cascades promoted by water.

Authors:  Ivan Vilotijevic; Timothy F Jamison
Journal:  Science       Date:  2007-08-31       Impact factor: 47.728

Review 8.  The chemistry of brevetoxins: a review.

Authors:  K Nakanishi
Journal:  Toxicon       Date:  1985       Impact factor: 3.033

9.  Brevenal is a natural inhibitor of brevetoxin action in sodium channel receptor binding assays.

Authors:  Andrea J Bourdelais; Susan Campbell; Henry Jacocks; Jerome Naar; Jeffery L C Wright; Jigani Carsi; Daniel G Baden
Journal:  Cell Mol Neurobiol       Date:  2004-08       Impact factor: 5.046

Review 10.  Natural and derivative brevetoxins: historical background, multiplicity, and effects.

Authors:  Daniel G Baden; Andrea J Bourdelais; Henry Jacocks; Sophie Michelliza; Jerome Naar
Journal:  Environ Health Perspect       Date:  2005-05       Impact factor: 9.031
  10 in total
  17 in total

1.  Characterization and localization of a hybrid non-ribosomal peptide synthetase and polyketide synthase gene from the toxic dinoflagellate Karenia brevis.

Authors:  Susanna López-Legentil; Bongkeun Song; Michael DeTure; Daniel G Baden
Journal:  Mar Biotechnol (NY)       Date:  2009-05-27       Impact factor: 3.619

Review 2.  The development of endo-selective epoxide-opening cascades in water.

Authors:  Christopher J Morten; Jeffery A Byers; Aaron R Van Dyke; Ivan Vilotijevic; Timothy F Jamison
Journal:  Chem Soc Rev       Date:  2009-09-16       Impact factor: 54.564

3.  A concise asymmetric total synthesis of (+)-brevisamide.

Authors:  Aaron T Herrmann; Steven R Martinez; Armen Zakarian
Journal:  Org Lett       Date:  2011-06-16       Impact factor: 6.005

4.  Absolute configuration of brevisamide and brevisin: confirmation of a universal biosynthetic process for Karenia brevis polyethers.

Authors:  Ryan M Van Wagoner; Masayuki Satake; Andrea J Bourdelais; Daniel G Baden; Jeffrey L C Wright
Journal:  J Nat Prod       Date:  2010-06-25       Impact factor: 4.050

5.  A Formal Total Synthesis of (-)-Brevisamide.

Authors:  Amos B Smith; Noriki Kutsumura; Justin Potuzak
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

6.  Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  RSC Adv       Date:  2016-11-24       Impact factor: 3.361

7.  Characterization of tamulamides A and B, polyethers isolated from the marine dinoflagellate Karenia brevis.

Authors:  Laura T Truxal; Andrea J Bourdelais; Henry Jacocks; William M Abraham; Daniel G Baden
Journal:  J Nat Prod       Date:  2010-04-23       Impact factor: 4.050

Review 8.  Biosynthesis and molecular genetics of polyketides in marine dinoflagellates.

Authors:  Ralf Kellmann; Anke Stüken; Russell J S Orr; Helene M Svendsen; Kjetill S Jakobsen
Journal:  Mar Drugs       Date:  2010-03-31       Impact factor: 5.118

Review 9.  Synthesis of marine polycyclic polyethers via endo-selective epoxide-opening cascades.

Authors:  Ivan Vilotijevic; Timothy F Jamison
Journal:  Mar Drugs       Date:  2010-03-19       Impact factor: 5.118

10.  An asymmetric total synthesis of brevisamide.

Authors:  Arun K Ghosh; Jianfeng Li
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005
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